Fungicidal acyl anilides

ABSTRACT

New acylanilides are disclosed which act as microbicides. They may preferably be used for combating phytopathogenic fungi.

This is a division of application Ser. No. 101,355 filed on Dec. 7,1979, now U.S. Pat. No. 4,294,850, which is a division of applicationSer. No. 923,604, filed on July 11, 1978, now U.S. Pat. No. 4,206,228.Application Ser. No. 923,604 was a division of application Ser. No.723,826, filed on Sept. 16, 1976, now U.S. Pat. No. 4,151,299, which wasa continuation of Ser. No. 565,037, filed on Apr. 4, 1975, nowabandoned.

The present invention provides compounds of the formula I ##STR1##wherein R₁ represents alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4carbon atoms or halogen, R₂ represents hydrogen, alkyl of 1 to 3 carbonatoms, alkoxy of 1 to 4 carbon atoms of halogen, R₇ represents hydrogen,alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 4 carbon atoms or halogen,R₈ represents hydrogen or methyl, the total number of carbon atoms ofthe substituents R₁, R₂, R₇ and R₈ in the phenyl ring not exceeding 8, Xrepresents ##STR2## wherein each of R', R" and R'" independentlyrepresents hydrogen, methyl, or ethyl, and Y represents one of thefollowing groups: ##STR3## wherein Hal is a halogen anion,

(b) --O--R₄,

(c) --S--R₄, wherein R₄ represents alkyl of 1 to 6 carbon atoms, alkenylof 3 to 6 carbon atoms, alkinyl of 3 to 6 carbon atoms, each of themunsubstituted or substituted by a halogen atom, or R₄ represents benzylof phenyl which independently may be unsubstituted or substituted byhalogen or alkyl of 1 to 4 carbon atoms or ##STR4## wherein each of R₅and R₆ independently represents alkyl of 1 to 4 carbon atoms. Theinvention also provides a process for the manufacture of these compoundsas well as compositions which contain them as active substances and amethod of using these active substances as microbicides.

By alkyl or alkyl moiety of an alkoxy group are meant the followinggroups, depending on the number of the indicated carbon atoms: methyl,ethyl, propyl, isopropyl, butyl, isobutyl, sec. butyl, tert. butyl aswell as pentyl and hexyl and the isomers thereof. Alkenyl of 3 to 6carbon atoms denotes above all allyl, methylallyl and pentenyl; andalkinyl of 3 to 6 carbon atoms is above all prop-2-inyl (propargyl) andbut-2-inyl.

By halogens, which can also appear in the hydrocarbon radicals of R₄,are meant fluorine, chlorine, bromine or iodine.

The present invention is based on the surprising observation thatcompounds with the structure of the formula I have for practicalpurposes a very favourable microbicidal spectrum for protectingcultivated plants. Examples of cultivated plants within the scope ofthis invention are: cereals, maize, rice, vegetables, sugar-beet, soya,ground nuts, fruit trees, ornamental plants, but principally vines,hops, cucumber plants (cucumber, marrows, melons) and solanaceae, suchas potatoes, tobacco and tomatoes, as well as banana, cocoa and rubberplants.

With the active substances of the formula I it is possible to destroythe fungi which occur in plants or parts of plants (fruit, blossoms,leaves, stems, tubers, roots) of these and also related cultivations ofuseful plants and also to protect from such fungi the parts of plantswhich grow later. The active substances act against the phytopathogenicfungi which belong to the following classes: ascomycetes (erysiphaceae);basidiomycetes, above all rust fungi, fungi imperfecti (moniliales); butespecially against the oomycetes which belong to the class of thephycomycetes, e.g. phytophthora, peronospora, pseudoperonospora, pythiumor plasmopara. In addition, the compounds of the formula I have asystemic action. They can also be used as seed dressing agents forprotecting seeds (fruit, tubers, grains) and plant cuttings from fungusinfections as well as from phytopathogenic fungi which occur in thesoil.

Preferred microbicides are compounds of the formula I in which R₁represents methyl, R₂ is in ortho-position to the amino group andrepresents methyl, ethyl or chlorine, --X--R₃ represents the group##STR5## and Y, R₇, R₈, R', R" and R'" have the meanings previouslyassigned to them. These compounds will be referred to as group Ia.

Compunds of the group Ia to be singled out for special mention onaccount of their action are those wherein R₇ represents hydrogen,methyl, chlorine or bromine, R₈ represents hydrogen or methyl, R'represents methyl, R" represents hydrogen or methyl and R'" representsmethyl or ethyl, and wherein Y represents one of the following groups:##STR6##

(b') --OR₄ or

(c') --SR₄, wherein R₄ represents alkyl of 1 to 4 carbon atoms, allyl,chloroallyl, 3-methylallyl, propargyl, phenyl, 4-methylphenyl,4-chlorophenyl, 2,4-dichlorophenyl, 4-tert. butylphenyl, benzyl or4-chlorobenzyl, ##STR7## wherein R₅ represents hydrogen or methyl and R₆represents methyl. These compounds will be referred to as group Ib.

An important group of microbicidal compounds belonging to this group Ibcomprises those compounds wherein each of R₇ and R₈ independentlyrepresents hydrogen or methyl, R' represents methyl, R" representshydrogen, R'" represents methyl or ethyl, and wherein Y represents --OR₄or --S--R₄, in which R₄ represents methyl, ethyl, propyl, isopropyl,butyl, sec. butyl or tert. butyl (group Ic).

An important subgroup of microbicidal compounds within the scope of theformula I comprises those of the formula Id ##STR8## wherein R₁represents alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atomsor halogen, R₂ represents hydrogen, alkyl of 1 to 3 carbon atoms orhalogen, X represents --CH₂ -- or ##STR9## and R₃ represents --COOR' or##STR10## wherein each of R', R" and R'" independently representshydrogen, methyl or ethyl, and Y represents one of the following groups:##STR11## wherein Hal is a halogen anion, --S--R₄, wherein R₄ representsalkyl of 1 to 6 carbon atoms or phenyl which is unsubstituted orsubstituted by halogen or alkyl of 1 to 4 carbon atoms, ##STR12##wherein each of R₅ and R₆ independently represents an alkyl radical of 1to 4 carbon atoms.

A further group of preferred compounds for regulating plant growthcomprises those compounds of the formula I in which R₁ represents methylor ethyl, R₂ is in ortho-position to the amino group and representsmethyl, ethyl or chlorine, --X--R₃ represents the group --CH₂--CON(R")(R'"), and Y represents --S--R₄ and R₄, R₇, R₈, R" and R'" havethe meanings previously assigned to them.

By plant growth regulation is meant primarily the retarding control ofnatural plant development, particularly the desirable reduction of thesize of the plant, especially the growth in height. This reduction ingrowth is observed in mono- and dicotyledonous plants, particularly ingrasses, cereal crops, soya or ornamental plants.

The compounds of the formula I are manufactured according to theinvention optionally

(A) by acylation of a compound of the formula II ##STR13## with acompound of the formula III ##STR14## or

(B) by initial monohaloacetylation of a compound of the formula II togive a compound of the formula IV ##STR15## and by further reactionoptionally with a compound of the formula V ##STR16## or with amercaptan (or the alkali or alkaline earth salt thereof) of the formula

    H--S--R.sub.4

or with thiourea.

In the formulae II, III, IV and V, the symbols R₁ to R₈ and X have themeanings assigned to them in the formula I, and Hal' represents halogen,preferably chlorine or bromine, and M represents a metal cation,preferably an alkali metal or alkaline earth metal cation.

The reactions can be carried out in the presence or absence of solventsof dilutents which are inert to the reactants. Examples of suitablesolvents or diluents are: aliphatic or aromatic hydrocarbons, e.g.benzene, toluene, xylene, petroleum ether; halogenated hydrocarbons,e.g. chlorobenzene, methylene chloride, ethylene chloride, chloroform;ethers and ethereal compounds, e.g. dialkyl ethers, dioxan,tetrahydrofuran; nitriles, e.g. acetonitrile; N,N-dialkylated amides,e.g. dimethyl formamide; anhydrous acetic acid, dimethyl sulphoxide,ketones, e.g. methyl ethyl ketone, and mixtures of such solvents.

The reaction temperatures are between 0° and 180° C., preferably between20° C. and 120° C. It is often advantageous to use acid acceptors orcondensation agents. Suitable examples are: tertiary amines, e.g.trialkylamines (e.g. triethylamine), pyridine and pyridine bases, orinorganic bases, e.g. the oxides and hydroxides, hydrogen carbonates andcarbonates of alkali metals and alkaline earth metals, as well as sodiumacetate. Moreover, in the first manufacturing method, it is alsopossible to use a surplus of the respective aniline derivative of theformula II as acid acceptor.

The process of manufacture A which proceeds from compounds of theformula II can also be carried out without acid acceptors; in someinstances it is expedient to pass in nitrogen in order to expel thehydrogen halide that has formed. In other instances it is veryadvantageous to use dimethyl formamide as reaction catalyst.

Particulars on the maufacture of the intermediates of the formula II canbe inferred from the methods which are generally indicated for themanufacture of anilinealkane acid esters in the following publications:

J. Org. Chem. 30, 4101 (1965); Tetrahedron 1967, 487; Tetrahedron 1967,493.

The compounds of the formula I in which X= ##STR17## contain anasymmetrical carbon atom (*) and can be resolved into the opticalantipodes in the customary manner. In this connection, the enantiomericD-form has the more pronounced microbicidal action.

Within the scope of the invention, those compounds, their compositionsand their use which refer to the D-configurations of the formula I areaccordingly preferred. These D-forms usually have in ethanol or acetonea negative angle of rotation.

The pure optical D-antipodes are obtained by manufacturing for examplethe racemic compound of the formula VI ##STR18## wherein R₁, R₂, R₇ andR₈ have the meanings assigned to them in formula I, and then reactingthe compound of the formula VI in known manner with anitrogen-containing, optically active base to give the correspondingsalt. The pure D-form is obtained stepwise by fractional crystallisationof the salt and subsequent liberation of the acid of the formula VIwhich is enriched with the optical D-antipode and, if appropriate,repeating (also several times) the salt formation, crystallisation andliberation of the α-anilino-propionic acid of the formula VI. From thispure D-form it is then possible, if desired, to manufacture in knownmanner, for example in the presence of HCl or H₂ SO₄, with methanol orethanol, the optical D-configuration of the ester falling under theformula II, or with the corresponding amine of formula HN(R")(R'"), theamide falling under the formula II, preferably via the acid halide. Asuitable optically active organic base is, for example,α-phenylethylamine.

Instead of the fractional crystallisation, it is also possible tomanufacture the enantiomeric D-form of the formula VII ##STR19## bydiazotising the amino group in the naturally occurring L-alanine in thepresence of e.g. HCl or HBr and thereby replacing it by halogenaccompanied by the splitting off of N₂ and with retention of theL-configuration, then, if appropriate, effecting esterification withmethanol or ethanol and subsequently reacting the ester with the anilineof the formula VIII ##STR20## when predominantly inversion to theD-configurations of the formula VII occurs (J. Am. Chem. Soc. 76, 6065).In the analogous manner it is also posible to manufacture in this mannerthe amides in which R₃ =CON(R")(R'"). Irrespective of the cited opticalisomerism, an atropisomerism is observed about the ##STR21## axis inthose instances in which the phenyl ring is substituted at least in2,6-position and at the same time unsymmetrically to this axis (i.e.also on account of the presence of additional substituents as the casemay be). This phenomenon is occasioned by the steric hindrance of theradicals --X--R₃ and --CO--R₄.

Also irrespective of the optical isomerism, where R₄ is alkenyl acis/trans-isomerism can occur in the double bond.

Provided no synthesis with the object of isolating pure isomers iscarried out, a product will normally occur as a mixture of two opticalisomers, two atropisomers, two cis/trans-isomers or as a mixture ofthese possible isomers. However, the basically better fungicidal actionof the enantiomeric D-form (in comparison to the D,L-form or to theL-form) is retained and is not noticeably affected by the atropisomerismor the cis/trans-isomerism.

The following Examples will serve to illustrate the invention in moredetail but do not limit it to what is described therein. Unless statedto the contrary, an active substance of the formula I, which can occurin optionally active form, is always to be understood as meaning theracemic mixture.

EXAMPLE 1 Manufacture of ##STR22##N-(1'-methoxycarbonyl-ethyl-N-methoxyacetyl-2,3-dimethyl-6-ethylaniline

(a) A mixture of 100 g of 2,3-dimethyl-6-ethylaniline, 223 g of2-bromopropionic acid methyl ester and 84 g of NaHCO₃ was stirred for 17hours at 140° C., then cooled, diluted with 300 ml of water andextracted with diethyl ether. The extract was washed with a small amountof water, dried over sodium sulphate, filtered and the ether wasevaporated. After the excess 2-bromopropionic acid methyl ester had beendistilled off, the crude product was distilled in a high vacuum; b.p.88°-90° C./0.04 Torr.

(b) A mixture of 11 g of the ester obtained according to (a), 6.5 g ofmethoxyacetyl chloride, 2 ml of dimethyl formamide and 250 ml of abs.toluene was stirred at room temperature and refluxed for 1 hour. Thesolvent was evaporated off and and the crude product then distilled invacuo; b.p. 126°-132° C./0.08 Torr.

The D-forms of both cis/trans-isomers (compounds 65 a and 65 b) areobtained by acylating the pure D-form ofα-(2,3-dimethyl-6-ethylanilino)-propionic acid methyl ester withmethoxyacetic acid or with one of the reactive derivatives thereof.

The other intermediates are also manufactured in a manner analogous tothat of Example 1a), including e.g. the following compounds of theformula IIa (R₁ =2-position): ##STR23##

    __________________________________________________________________________                                  Physical constant                               R.sub.1                                                                             R.sub.2                                                                            R.sub.5                                                                             --X--R.sub.3 (temperatures in °C.)                    __________________________________________________________________________    CH.sub.3                                                                            CH.sub.3                                                                           H     --CH(CH.sub.3)--COOCH.sub.3                                                                b.p. 98° C./0.8 Torr                     CH.sub.3                                                                            C.sub.2 H.sub.5                                                                    H     "            b.p. 88°-90° C./0.01 Torr         CH.sub.3                                                                            C.sub.2 H.sub.5                                                                    5-CH.sub.3                                                                          "            b.p. 96°-99° C./0.03 Torr         CH.sub.3                                                                            CH.sub.3                                                                           3-CH.sub.3                                                                          "            b.p. 83° C./0.03 Torr;                                                 145° C./9 Torr                           CH.sub.3                                                                            CH.sub.3                                                                           4-CH.sub.3                                                                          "            b.p. 88°-90° C./0.04 Torr         CH.sub.3                                                                            C.sub.2 H.sub.5                                                                    3-CH.sub.3                                                                          "            b.p. 88°-90° C./0.04 Torr         CH.sub.3                                                                            H    4-CH.sub.3                                                                          "            b.p. 95°-100° C./0.02 Torr        CH.sub.3                                                                            H    5-CH.sub.3                                                                          "            b.p. 106°-108° C./0.1 Torr        CH.sub.3                                                                            H    3-CH.sub.3                                                                          "            b.p. 146° C./5 Torr                      isoC.sub.3 H.sub.7                                                                  H    H     "            b.p. 110° C./0.2 Torr                    isoC.sub.3 H.sub.7                                                                  isoC.sub.3 H.sub.7                                                                 H     "            b.p. 105° C./0.5 Torr                    t.C.sub.4 H.sub.9                                                                   H    H     "            b.p. 93° C./0.07 Torr                    CH.sub.3                                                                            H    4-Cl  "            b.p. 125°-127° C./0.07 Torr       CH.sub.3                                                                            Cl   H     "            b.p. 88°-89° C./0.03 Torr         CH.sub.3                                                                            CH.sub.3                                                                           4-Br  "            m.p. 31.5°-32.5°                  CH.sub.3                                                                            CH.sub.3                                                                           3-Br  "            m.p. 46°-47.5° C.                 F     H    H     "            b.p. 98° C./0.15 Torr                    Cl    H    H     "            b.p. 90°-100° C./0.09 Torr        Br    H    H     "            b.p. 110° C./0.01 Torr                   CH.sub.3                                                                            CH.sub.3                                                                           4-I   "            m.p. 81°-83° C.                   I     H    H     "            b.p. 105° C./0.15 Torr                   nC.sub.4 H.sub.9 O--                                                                H    H     "            b.p. 132° C./0.5 Torr                    CH.sub.3                                                                            H    4-CH.sub.3 O--                                                                      "            b.p. 131° C./0.5 Torr                    CH.sub.3                                                                            H    4 sec.-                                                                             "            b.p. 138° C./0.15 Torr                              C.sub.4 H.sub.9 O--                                                Cl    H    5-Cl  "            m.p. 51.5°-54° C.                 CH.sub.3                                                                            C.sub.2 H.sub.5                                                                    H     --CH(CH.sub.3)--CONH.sub.2                                                                 b.p. 155°-157°  C./0.1 Torr       C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                                    H     --CH(CH.sub.3)--CONH.sub.2                                                                 m.p. 71°-73° C.                   C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                                    H     --CH.sub.2 --CONH.sub.2                                                                    m.p. 103°--106° C.                C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                                    H     --CH.sub.2 --COOC.sub.2 H.sub.5                                                            b.p. 100°-103° C./0.04 Torr       C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                                    H     --CH.sub.2 --CON(CH.sub.3).sub.2                                                           wax-like                                        CH.sub.3                                                                            CH.sub.3                                                                           H     --CH.sub.2 --CONH.sub.2                                                                    m.p. 89°-91° C.                   CH.sub.3                                                                            CH.sub.3                                                                           H     --CH(CH.sub.3)--CONH.sub.2                                                                 m.p. 102°-103° C.                 CH.sub.3                                                                            CH.sub.3                                                                           H     --CH(CH.sub.3)--CONHCH.sub.3                                                               m.p. 75°-76° C.                   CH.sub.3                                                                            CH.sub.3                                                                           H     --CH(CH.sub.3)--CON(CH.sub.3).sub.2                                                        b.p. 104°-108° C./0.02 Torr       C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                                    H     --CH.sub.2 --CONHCH.sub.3                                                                  m.p. 59°-61.5° C.                 C.sub.2 H.sub.5                                                                     C.sub.2 H.sub.5                                                                    H     --CH.sub.2 --CONHC.sub.2 H.sub.5                             m.p. 79°m.p. 80°  C.                                            CH.sub.3                                                                            CH.sub.3                                                                           H     --CH.sub.2 --COOCH.sub.3                                                                   b.p. 155°-160° C./20 Torr         CH.sub.3                                                                            Cl   H     --CH(CH.sub.3)--COOC.sub.2 H.sub.5                                                         b.p. 110°-120° C./0.3 Torr        CH.sub.3                                                                            C.sub.2 H.sub.5                                                                    H     --CH.sub.2 --COOCH.sub.3                                                                   b.p. 168° -171° C./30 Torr        CH.sub.3                                                                            Cl   H     --CH(CH.sub.3)--CONHCH.sub.3                                                               m.p. 51°-53° C.                   CH.sub.3                                                                            Cl   4-I   --CH(CH.sub.3)--COOCH.sub.3                                                                m.p. 118°-122° C.                 CH.sub.3                                                                            CH.sub.3                                                                           4-Cl  --CH(CH.sub.3)--COOCH.sub.3                                                                m.p. 135°-137° C./0.02 Torr       CH.sub.3                                                                            C.sub.2 H.sub.5                                                                    4-I   --CH(CH.sub.3)--COOCH.sub.3                                                                m.p. 65°-69° C.                   CH.sub.3                                                                            C.sub.2 H.sub.5                                                                    4-Cl  --CH(CH.sub.3)--COOCH.sub.3                                                                b.p. 142°-145° C./0.04 Torr       CH.sub.3                                                                            Cl   4-Cl  --CH(CH.sub.3)--COOCH.sub.3                                                                b.p. 151°-153° C./0.03 Torr       CH.sub.3                                                                            Cl   4-Br  --CH(CH.sub.3)--COOCH.sub.3                                                                m.p. 82°-85° C.                   CH.sub.3                                                                            C.sub.2 H.sub.5                                                                    4-Br  --CH(CH.sub.3)--COOCH.sub.3                                                                m.p. 52°-54° C.                   __________________________________________________________________________

EXAMPLE 2 Manufacture of ##STR24##N-(1'-methoxycarbonyl-ethyl)-N-([N'N'-dimethyldithiocarbamoyl]-methylcarbonyl)-2,6-dimethylaniline

(a) Manufacture ofN-(1'-methoxycarbonyl-ethyl)-N-chloroacetyl-2,6-dimethylaniline.

990.3 g (4.76 g-moles) of α-(2,6-dimethylanilino)-propionic acid methylester are mixed with 605 g (5.7 g-moles) of sodium carbonate in 2.5liters of abs. benzene. To this mixture are then added slowly dropwise455 ml (5.7 g-moles) of monochloroacetyl chloride in such a way that atemperature of 30°-35° C. in the reaction mixture is not exceeded. Afterit has stirred at room temperature overnight, the mixture is filteredoff and the filtrate is concentrated by rotary evaporation at c. 50° C.The residue is recrystallised from petroleum ether (boiling range65°-90° C.). Yield: 1132 g of intermediate (m.p. 92°-94° C.).

(b) A mixture of 85.2 g of the α-propionic acid methyl ester obtainedaccording to (a) and 53.7 g of sodium dimethyldithiocarbamate in 1000 mlof acetonitrile was refluxed for 6 hours with stirring and passing innitrogen. After it had been cooled, the reaction mixture was drownedinto water and the reaction product was extracted with chloroform. Thechloroform was evaporated off and the product recrystallised frommethanol. The white crystals of compound No. 374 melt between127°-128.5° C.

EXAMPLE 3 Manufacture of ##STR25##N-(1'-methoxycarbonylethyl)-N-([isothiuronium-hydrochloride-S-]-methylcarbonyl)-2,6-dimethylaniline

A mixture of 21.8 g ofN-(1'-methoxycarbonyl-ethyl)-N-chloroacetyl-2,6-dimethylaniline and 5.4g of thiourea was refluxed for 1 hour with stirring and the reactionproduct precipitated from the solution. The batch was cooled and theproduct filtered off and recrystallised from isopropanol.

The white crystals of compound No. 378 melt between 258°-260° C. withdecomposition.

The following compounds of the formula ##STR26## were manufactured inanalogous manner: (R₁ =2-position).

    __________________________________________________________________________    Com-                              Physical constant                           pound                                                                             R.sub.1                                                                            R.sub.2                                                                             R.sub.7                                                                             Z.sub.1      (temperatures in °C.)                __________________________________________________________________________    1   CH.sub.3                                                                           6-CH.sub.3                                                                          H     CH.sub.3     m.p. 67°-68° C.               2   CH.sub.3                                                                           6-CH.sub.3                                                                          H     C.sub.2 H.sub.5                                                                            b.p. 130°-132° C./0.02                                          Torr                                        3   CH.sub.3                                                                           6-CH.sub.3                                                                          H     n-C.sub.3 H.sub.7                                                                          b.p. 133°-140° C./0.03                                          Torr                                        4   CH.sub.3                                                                           6-CH.sub.3                                                                          H     isoC.sub.3 H.sub.7                                                                         b.p. 137°-140° C./0.04                                          Torr                                        5   CH.sub.3                                                                           6-CH.sub.3                                                                          H     sec.C.sub.4 H.sub.9                                                                        b.p. 141°-143° C./0.04                                          Torr                                        6   CH.sub.3                                                                           6-CH.sub.3                                                                          H     tert.C.sub.4 H.sub.9                                     7   CH.sub.3                                                                           6-CH.sub.3                                                                          H     n-C.sub.4 H.sub.9                                                                          b.p. 145°-147° C./0.03                                          Torr                                        8   CH.sub.3                                                                           6-CH.sub.3                                                                          H     sec.C.sub.5 H.sub.11                                     9   CH.sub.3                                                                           6-C.sub.2 H.sub.5                                                                   H     CH.sub.3     b.p. 138°-139° C./0.07                                          Torr                                        10  CH.sub.3                                                                           6-C.sub.2 H.sub.5                                                                   H     C.sub.2 H.sub.5                                                                            b.p. 140°-142° C./0.04                                          Torr                                        11  CH.sub.3                                                                           6-C.sub.2 H.sub.5                                                                   H     isoC.sub.3 H.sub. 7                                                                        b.p. 148° C./0.4 Torr                12  CH.sub.3                                                                           6-C.sub.2 H.sub.5                                                                   H     sec.C.sub.4 H.sub.9                                                                        b.p. 141°-144° C./0.05                                          Torr                                        13  CH.sub.3                                                                           6-C.sub.2 H.sub.5                                                                   H     tert.C.sub.4 H.sub.9                                     14  CH.sub.3                                                                           6-C.sub.2 H.sub.5                                                                   H     nC.sub.4 H.sub.9                                         15  CH.sub.3                                                                           6-C.sub.2 H.sub.5                                                                   H     sec.C.sub.5 H.sub.11                                     16  CH.sub.3                                                                           6-Cl  H     CH.sub.3     m.p. 47°-56° C.               17  CH.sub.3                                                                           6-Cl  H     C.sub.2 H.sub.5                                                                            b.p. 148°-150° C./0.04                                          Torr                                        18  CH.sub.3                                                                           6-Cl  H     isoC.sub.3 H.sub.7                                                                         b.p. 147° C./0.15 Torr               19  CH.sub.3                                                                           6-Cl  H     tert.C.sub.4 H.sub.9                                     20  CH.sub.3                                                                           6-Cl  H     sec.C.sub.4 H.sub.9                                                                        b.p. 153°-155° C./0.07                                          Torr                                        21  CH.sub.3                                                                           6-Cl  H     sec.C.sub.5 H.sub.11                                     22  CH.sub.3                                                                           5-CH.sub.3                                                                          H     CH.sub.3                                                 23  CH.sub.3                                                                           5-CH.sub.3                                                                          H     C.sub.2 H.sub.5                                          24  CH.sub.3                                                                           5-CH.sub.3                                                                          H     isoC.sub.3 H.sub.7                                                                         b.p. 147° C./0.3 Torr                25  C.sub.2 H.sub.5                                                                    6-C.sub.2 H.sub.5                                                                   H     CH.sub.3     b.p. 142°-145° C./0.06                                          Torr                                        26  C.sub.2 H.sub.5                                                                    6-C.sub.2 H.sub.5                                                                   H     C.sub.2 H.sub.5                                          27  C.sub.2 H.sub.5                                                                    6-C.sub.2 H.sub.5                                                                   H     isoC.sub.3 H.sub.7                                                                         b.p. 152° C./0.1 Torr                28  CH.sub.3                                                                           3-CH.sub.3                                                                          6-CH.sub.3                                                                          CH.sub.3     m.p. 58°-68° C.               29  CH.sub.3                                                                           3-CH.sub.3                                                                          6-CH.sub.3                                                                          C.sub.2 H.sub.5                                                                            b.p. 140 °-142° C./0.04                                         Torr                                        30  CH.sub.3                                                                           3-CH.sub.3                                                                          6-CH.sub.3                                                                          n-C.sub.3 H.sub.7                                                                          b.p. 138°-140° C./0.06                                          Torr                                        31  CH.sub.3                                                                           3-CH.sub.3                                                                          6-CH.sub.3                                                                          isoC.sub.3 H.sub.7                                                                         b.p. 140°-142° C./0.08                                          Torr                                        32  CH.sub.3                                                                           3-CH.sub.3                                                                          6-CH.sub.3                                                                          n-C.sub.4 H.sub.9                                                                          b.p. 147°-148° C./0.06                                          Torr                                        33  CH.sub.3                                                                           3-CH.sub.3                                                                          6-CH.sub.3                                                                          sec.C.sub.4 H.sub.9                                                                        b.p. 150°-152° C./0.06                                          Torr                                        34  CH.sub.3                                                                           3-CH.sub.3                                                                          6-CH.sub.3                                                                          tert.C.sub.4 H.sub.9                                     35  CH.sub.3                                                                           3-CH.sub.3                                                                          6-CH.sub.3                                                                          sec.C.sub.5 H.sub.11                                                                       b.p. 159°-161° C./0.04                                          Torr                                        36  CH.sub.3                                                                           4-CH.sub.3                                                                          6-CH.sub.3                                                                          CH.sub.3     m.p. 50°-53° C.               37  CH.sub.3                                                                           4-CH.sub.3                                                                          6-CH.sub.3                                                                          C.sub.2 H.sub.5                                                                            b.p. 148°-151° C./0.08                                          Torr                                        38  CH.sub.3                                                                           4-CH.sub.3                                                                          6-CH.sub.3                                                                          isoC.sub.3 H.sub.7                                                                         b.p. 149°-152° C./0.07                                          Torr                                        39  CH.sub.3                                                                           4-CH.sub.3                                                                          6-CH.sub.3                                                                          sec.C.sub.4 H.sub.9                                                                        b.p. 157°-159° C./0.08                                          Torr                                        40  CH.sub.3                                                                           4-CH.sub.3                                                                          6-CH.sub.3                                                                          sec.C.sub.5 H.sub.11                                     41  CH.sub.3                                                                           5-CH.sub.3                                                                          6-C.sub.2 H.sub.5                                                                   CH.sub.3                                                 42  CH.sub.3                                                                           5-CH.sub.3                                                                          6-C.sub.2 H.sub.5                                                                   C.sub.2 H.sub.5                                          43  CH.sub.3                                                                           5-CH.sub.3                                                                          6-C.sub.2 H.sub.5                                                                   isoC.sub.3 H.sub.7                                       44  CH.sub.3                                                                           3-Br  6-CH.sub.3                                                                          CH.sub.3     b.p. 200° C./0.04 Torr               45  CH.sub.3                                                                           3-Br  6-CH.sub.3                                                                          C.sub.2 H.sub.5                                          46  CH.sub.3                                                                           3-Br  6-CH.sub.3                                                                          isoC.sub.3 H.sub.7                                       47  CH.sub.3 O--                                                                       6-CH.sub.3                                                                          H     CH.sub.3                                                 48  CH.sub.3 O--                                                                       6-CH.sub.3                                                                          H     isoC.sub.3 H.sub.7                                       49  CH.sub.3 O--                                                                       4-CH.sub.3 O--                                                                      6-CH.sub.3 0--                                                                      CH.sub.3                                                 50  Cl   6-Cl  H     CH.sub.3     b.p. 180°-182° C./0.04                                          Torr                                        51  Cl   6-Cl  H     C.sub.2 H.sub.5                                          52  Cl   6-Cl  H     isoC.sub.3 H.sub.7                                       53  F    H     H     CH.sub.3                                                 54  F    H     H     isoC.sub.3 H.sub.7                                                                         b.p. 130° C./0.01 Torr               55  F    H     H     sec.C.sub.4 H.sub.9                                                                        b.p. 130°-137° C./0.04                                          Torr                                        56  Cl   H     H     CH.sub.3                                                 57  Cl   H     H     isoC.sub.3 H.sub.7                                                                         b.p. 130° C./0.05 Torr               58  I    H     H     CH.sub.3                                                 59  I    H     H     isoC.sub.3 H.sub.7                                                                         b.p. 168° C./0.3 Torr                60  Br   H     H     C.sub.2 H.sub.5                                          61  Br   H     H     isoC.sub.3 H.sub.7                                       62  CH.sub.3                                                                           3-CH.sub.3                                                                          H     CH.sub.3     b.p. 140° C./0.04 Torr               63  CH.sub.3                                                                           3-CH.sub.3                                                                          H     C.sub.2 H.sub.5                                          64  CH.sub.3                                                                           3-CH.sub.3                                                                          H     isoC.sub.3 H.sub.7                                       65  CH.sub.3                                                                           3-CH.sub.3                                                                          6-C.sub.2 H.sub.5                                                                   CH.sub.3     b.p. 126°-132° C./0.08                                          Torr                                        66  CH.sub.3                                                                           3-CH.sub.3                                                                          6-C.sub.2 H.sub.5                                                                   C.sub.2 H.sub.5                                          67  CH.sub.3                                                                           3-CH.sub.3                                                                          6-C.sub.2 H.sub.5                                                                   iso-C.sub.3 H.sub.7                                      68  CH.sub.3                                                                           3-CH.sub.3                                                                          6-C.sub.2 H.sub.5                                                                   secC.sub.4 H.sub.9                                       69  CH.sub.3                                                                           4-sec.-                                                                             H     CH.sub.3                                                          C.sub.4 H.sub.9 O--                                                  70  CH.sub.3                                                                           4-sec.-                                                                             H     C.sub.2 H.sub.5                                                   C.sub.4 H.sub.9 O                                                    71  CH.sub.3                                                                           4-sec.-                                                                             H     isoC.sub.3 H.sub.7                                                                         b.p. 175° C./0.3 Torr                         C.sub.4 H.sub.9 O                                                    72  CH.sub.3                                                                           4-CH.sub.3 O--                                                                      H     CH.sub.3                                                 73  C.sub.2 H.sub.5                                                                    6-Cl  H     CH.sub.3                                                 74  C.sub.2 H.sub.5                                                                    6-Cl  H     isoC.sub.3 H.sub.7                                       75  CH.sub.3                                                                           6-CH.sub.3                                                                          H     --CH.sub.2 --CH═CH.sub.2                                                               b.p. 151°-153° C./0.04                                          Torr                                        76  CH.sub.3                                                                           6-Cl  H     --CH.sub.2 --CH═CH.sub.2                                                               b.p. 162°-164° C./0.04                                          Torr                                        77  CH.sub.3                                                                           6-C.sub.2 H.sub.5                                                                   H     --CH.sub.2 --CH═CH.sub.2                                                               b.p. 150°-152° C./0.06                                          Torr                                        78  C.sub.2 H.sub.5                                                                    6-C.sub.2 H.sub.5                                                                   H     --CH.sub.2 --CH═CH.sub.2                             79  CH.sub.3                                                                           4-CH.sub.3                                                                          H     --CH.sub.2 --CH═CH.sub.2                             80  C.sub.2 H.sub.5                                                                    6-Cl  H     --CH.sub.2 --CH═CH.sub.2                             81  CH.sub.3                                                                           3-CH.sub.3                                                                          6-CH.sub.3                                                                          --CH.sub.2 --CH═CH.sub.2                             82  CH.sub.3                                                                           4-CH.sub.3                                                                          6-CH.sub.3                                                                          --CH.sub.2 --CH═CH.sub.2                             83  Cl   6-Cl  H     --CH.sub.2 --CH═CH.sub.2                             84  F    H     H     --CH.sub.2 --CH═CH.sub.2                                                               b.p. 129° C./0.05 Torr               85  Cl   H     H     -- CH.sub.2 --CH═CH.sub.2                            86  CH.sub.3                                                                           6-CH.sub.3                                                                          H     --CH.sub.2 --C(CH.sub.3)═CH.sub.2                                                      b.p. 158°-160° C./0.02                                          Torr                                        87  CH.sub.3                                                                           4-CH.sub.3                                                                          6-CH.sub.3                                                                          --CH.sub.2 --CH═CH--CH.sub.3                         88  CH.sub.3                                                                           3-CH.sub.3                                                                          6-CH.sub.3                                                                          --CH.sub.2 --CH═CH--CH.sub.3                         89  CH.sub.3                                                                           6-C.sub.2 H.sub.5                                                                   H     --CH.sub.2 --CH═CH--CH.sub.3                         90  CH.sub.3                                                                           6-CH.sub.3                                                                          H     --CH.sub.2 --CH═CH--CH.sub.3                         91  CH.sub.3                                                                           6-Cl  H     --CH.sub.2 --CH═CH--CH.sub.3                         92  CH.sub.3                                                                           6-CH.sub.3                                                                          H     --C.sub.6 H.sub.5                                                                          b.p. 175° C./0.04 Torr               93  CH.sub.3                                                                           6-Cl  H     --C.sub.6 H.sub.5                                        94  CH.sub.3                                                                           6-C.sub.2 H.sub.5                                                                   H     --C.sub.6 H.sub.5                                                                          b.p. 178°-180° C./0.05                                          Torr                                        95  CH.sub.3                                                                           4-CH.sub.3                                                                          H     --C.sub.6 H.sub.5                                        96  C.sub.2 H.sub.5                                                                    6-Cl  H     --C.sub.6 H.sub.5                                        97  CH.sub.3                                                                           3-CH.sub.3                                                                          6-CH.sub.3                                                                          --C.sub.6 H.sub.5                                                                          b.p. 182°-184° C./0.05                                          Torr                                        98  CH.sub.3                                                                           4-CH.sub.3                                                                          6-CH.sub.3                                                                          --C.sub.6 H.sub. 5                                                                         b.p. 187°-189° C./0.04                                          Torr                                        99  CH.sub.3                                                                           3-CH.sub.3                                                                          6-C.sub.2 H.sub.5                                                                   --C.sub.6 H.sub.5                                        100 CH.sub.3                                                                           5-CH.sub.3                                                                          6-C.sub.2 H.sub.5                                                                   --C.sub.6 H.sub.5                                        101 C.sub.2 H.sub.5                                                                    5-s.  H     --C.sub.6 H.sub.5                                                 C.sub.4 H.sub.9 O--                                                  102 Cl   6-Cl  H     --C.sub.6 H.sub.5                                        103 Cl   6-Br  H     --C.sub.6 H.sub.5                                        104 Cl   H     H     --C.sub.6 H.sub.5                                        105 F    H     H     --C.sub.6 H.sub.5                                                                          m.p. 37°-40° C.               106 Br   H     H     --C.sub.6 H.sub.5                                        107 I    H     H     --C.sub.6 H.sub.5                                        108 CH.sub.3                                                                           6-CH.sub.3                                                                          H     --C.sub.6 H.sub.3 Cl.sub.2 (2,4)                                                           m.p. 101°-104° C.             109 CH.sub.3                                                                           6-Cl  H     --C.sub.6 H.sub.3 Cl.sub.2 (2,4)                         110 CH.sub.3                                                                           6-C.sub.2 H.sub.5                                                                   H     --C.sub.6 H.sub.3 Cl.sub.2 (2,4)                         111 CH.sub.3                                                                           4-CH.sub.3                                                                          6-CH.sub.3                                                                          --C.sub.6 H.sub.3 Cl.sub.2 (2,4)                         112 CH.sub.3                                                                           3-CH.sub.3                                                                          6-CH.sub.3                                                                          --C.sub.6 H.sub.3 Cl.sub.2 (2,4)                         113 CH.sub.3 O--                                                                       6-C.sub.2 H.sub.5                                                                   H     --C.sub.6 H.sub.3 Cl.sub.2 (2,4)                         114 F    H     H     --C.sub.6 H.sub.3 Cl.sub.2 (2,4)                                                           m.p. 133°-136° C.             115 Cl   H     H     --C.sub.6 H.sub.3 Cl.sub.2 (2,4)                         116 Cl   6-Cl  H     --C.sub.6 H.sub.3 Cl.sub.2 (2,4)                         117 Cl   3-CH.sub.3                                                                          6-Cl  --C.sub.6 H.sub.3 Cl.sub.2 (2,4)                         118 CH.sub.3                                                                           6-CH.sub.3                                                                          H     --CH.sub.2 --C.sub.6 H.sub.5                                                               m.p. 81°-86° C.               119 CH.sub.3                                                                           6-Cl  H     --CH.sub.2 --C.sub.6 H.sub.5                             120 CH.sub.3                                                                           3-CH.sub.3                                                                          6-CH.sub.3                                                                          --CH.sub.2 --C.sub.6 H.sub.5                                                               b.p. 180°-182° C./0.03                                          Torr                                        121 CH.sub.3                                                                           4-CH.sub.3                                                                          6-CH.sub.3                                                                          --CH.sub.2 --C.sub.6 H.sub.5                             122 CH.sub.3                                                                           6-C.sub.2 H.sub.5                                                                   H     --CH.sub.2 H.sub.5                                       123 Cl   H     H     --CH.sub.2 --C.sub.6 H.sub.5                             124 Cl   6-Cl  H     --CH.sub.2 --C.sub.6 H.sub.5                             125 CH.sub.3                                                                           6-CH.sub.3                                                                          H     --CH.sub.2 --C.sub.6 H.sub.4 --Cl(4)                                                       b.p. 187°-189° C./0.04                                          Torr                                        126 CH.sub. 3                                                                          6-CH.sub.3                                                                          H     --CH.sub.2 --C.sub.6 H.sub.3 Cl.sub.2 (3,4)              127 CH.sub.3                                                                           6-CH.sub.3                                                                          H     --CH(CH.sub.3)--C.tbd.CH                                 128 CH.sub.3                                                                           6-Cl  H     --CH(CH.sub.3)--C.tbd.CH                                 129 Cl   6-Cl  H     --CH(CH.sub.3)--C.tbd.CH                                 130 CH.sub.3                                                                           3-CH.sub.3                                                                          6-CH.sub.3                                                                          --CH(CH.sub.3)--C.tbd.CH                                                                   viscous oil                                 131 CH.sub.3                                                                           4-CH.sub.3                                                                          6-CH.sub.3                                                                          --CH(CH.sub.3)--C.tbd.CH                                                                   viscous oil                                 132 CH.sub.3                                                                           6-C.sub.2 H.sub.5                                                                   H     --CH(CH.sub.3)--C.tbd.CH                                 133 CH.sub.3                                                                           4-CH.sub.3                                                                          6-CH.sub.3                                                                          --CH.sub.2 --C.tbd.CH                                    134 CH.sub.3                                                                           6-CH.sub.3                                                                          H     --CH.sub.2 --C.tbd.CH                                                                      viscous oil                                 135 CH.sub.3                                                                           6-Cl  H     --CH.sub.2 --C.tbd.CH                                    136 CH.sub.3                                                                           3-CH.sub.3                                                                          6-CH.sub.3                                                                          --CH.sub.2 --C.tbd.CH                                    137 CH.sub.3                                                                           6-C.sub.2 H.sub.5                                                                   H     --CH.sub.2 --C.tbd.CH                                    138 CH.sub.3                                                                           6-Cl  H     --CH.sub.2 --C.tbd.CI                                    139 CH.sub.3                                                                           4-CH.sub.3                                                                          6-CH.sub.3                                                                          --CH.sub.2 --C.tbd.CI                                    140 CH.sub.3                                                                           6-CH.sub.3                                                                          H     --CH.sub.2 --C.tbd.CI                                                                      m.p. 58°-60° C.               141 CH.sub.3                                                                           3-CH.sub.3                                                                          6-CH.sub.3                                                                          --CH.sub.2 --C.tbd.CI                                    142 CH.sub.3                                                                           6-CH.sub.3                                                                          H     --CH(CH.sub.3)--C.tbd.CI                                 143 CH.sub.3                                                                           6-C.sub.2 H.sub.5                                                                   H     --CH.sub.2 --C.tbd.CI                                    144 CH.sub.3                                                                           4-Cl  6-CH.sub.3                                                                          CH.sub.3     m.p. 87°-90° C.               145 CH.sub.3                                                                           4-Cl  6-CH.sub.3                                                                          C.sub.2 H.sub.5                                          146 CH.sub.3                                                                           4-Cl  6-CH.sub.3                                                                          nC.sub.3 H.sub.7                                         147 CH.sub.3                                                                           4-Cl  6-CH.sub.3                                                                          isoC.sub.3 H.sub.7                                       148 CH.sub.3                                                                           4-Cl  6-CH.sub.3                                                                          sec.C.sub.4 H.sub.9                                                                        m.p. 75°-78° C.               149 CH.sub.3                                                                           4-Cl  6-CH.sub.3                                                                          tert.C.sub.4 H.sub.9                                     150 CH.sub.3                                                                           4-Cl  6-CH.sub.3                                                                          nC.sub.5 H.sub.11                                        151 CH.sub.3                                                                           4-Cl  6-CH.sub.3                                                                          --C.sub.6 H.sub.5                                        152 CH.sub.3                                                                           4-Cl  6-CH.sub.3                                                                          --CH.sub.2 C.sub.6 H.sub.5                               153 CH.sub.3                                                                           4-Br  6-CH.sub.3                                                                          --C.sub.6 H.sub.4 CH.sub.3 (4)                           154 CH.sub.3                                                                           4-Br  6-CH.sub.3                                                                          --C.sub.6 H.sub.4 CH.sub.3 (2)                           155 CH.sub.3                                                                           4-Br  6-CH.sub.3                                                                          CH.sub.3     m.p. 98°-100° C.              156 CH.sub.3                                                                           4-Br  6-CH.sub.3                                                                          C.sub.2 H.sub.5                                                                            m.p. 64°-65.5° C.             157 CH.sub.3                                                                           4-Br  6-CH.sub.3                                                                          --CH.sub.2 CH═CH.sub.2                                                                 m.p. 38.5°-41° C.             158 CH.sub.3                                                                           4-Br  6-CH.sub.3                                                                          sec.C.sub.4 H.sub.9                                                                        m.p. 51°-53.5° C.             159 CH.sub.3                                                                           4-Br  6-CH.sub.3                                                                          --C.sub.6 H.sub.5                                                                          m.p. 110°-111° C.             160 CH.sub.3                                                                           4-Br  6-CH.sub.3                                                                          --CH.sub.2 C.sub.6 H.sub.5                               161 CH.sub.3                                                                           4-Br  6-CH.sub.3                                                                          isoC.sub.3 H.sub.7                                       162 CH.sub.3                                                                           4-Br  6-CH.sub.3                                                                          nC.sub.4 H.sub.9                                         163 CH.sub.3                                                                           4-Br  6-CH.sub.3                                                                          C.sub.6 H.sub.3 Cl.sub.2 (3,5)                           164 CH.sub.3                                                                           4-Br  6-CH.sub.3                                                                          n-C.sub.3 H.sub.7                                        165 CH.sub.3                                                                           4-Br  6-CH.sub.3                                                                          tert.C.sub.4 H.sub.9                                     166 CH.sub.3                                                                           4-Br  6-CH.sub.3                                                                          nC.sub.5 H.sub.11                                        167 CH.sub.3                                                                           4-Br  6-CH.sub.3                                                                          --CH.sub.2 C.sub.6 H.sub.5                               168 CH.sub.3                                                                           4-I   6-CH.sub.3                                                                          CH.sub.3     m.p. 82°-84° C.               169 CH.sub.3                                                                           4-I   6-CH.sub.3                                                                          C.sub.2 H.sub.5                                          170 CH.sub.3                                                                           4-I   6-CH.sub.3                                                                          n-C.sub.3 H.sub.7                                        171 CH.sub.3                                                                           4-I   6-CH.sub.3                                                                          isoC.sub.3 H.sub.7                                       172 CH.sub.3                                                                           4-I   6-CH.sub.3                                                                          sec.C.sub.4 H.sub.9                                      173 CH.sub.3                                                                           4-I   6-CH.sub.3                                                                          --CH.sub.2 --CH═CH.sub.2                             174 CH.sub.3                                                                           4-I   6-CH.sub.3                                                                          C.sub.6 H.sub.5                                          175 CH.sub.3                                                                           4-I   6-CH.sub.3                                                                          C.sub.6 H.sub.3 Cl.sub.2 (3,5)                           176 CH.sub.3                                                                           4-Cl  6-C.sub.2 H.sub.5                                                                   CH.sub.3                                                 177 CH.sub.3                                                                           4-Cl  6-Cl  CH.sub.3     m.p. 105°-108° C.             178 CH.sub.3                                                                           4-Cl  6-C.sub.2 H.sub.5                                                                   C.sub.2 H.sub.5                                          179 CH.sub.3                                                                           4-Cl  6-C.sub.2 H.sub.5                                                                   isoC.sub.3 H.sub.7                                       180 CH.sub.3                                                                           4-Cl  6-C.sub.2 H.sub.5                                                                   sec.C.sub.4 H.sub.9                                      181 CH.sub.3                                                                           4-Cl  CH.sub.3                                                       182 CH.sub.3                                                                           4-Br  6-C.sub.2 H.sub.5                                                                   C.sub.2 H.sub.5                                          183 CH.sub.3                                                                           4-Br  6-C.sub.2 H.sub.5                                                                   CH.sub.3     m.p. 87°-90° C.               184 CH.sub.3                                                                           4-Br  6-C.sub.2 H.sub.5                                                                   isoC.sub.3 H.sub.7                                       185 CH.sub.3                                                                           4-Br  6-Cl  CH.sub.3                                                 186 CH.sub.3                                                                           4-Cl  6-Cl  C.sub.2 H.sub.5                                          187 CH.sub.3                                                                           4-I   6-C.sub.2 H.sub.5                                                                   isoC.sub.3 H.sub.7                                       188 CH.sub.3                                                                           4-I   6-C.sub.2 H.sub.5                                                                   C.sub.4 H.sub.3 Cl.sub.2 (3,5)                           189 CH.sub.3                                                                           4-Br  6-Cl  C.sub.6 H.sub.5                                          190 CH.sub.3                                                                           4-Br  6-C.sub.2 H.sub.5                                                                   sec.C.sub.4 H.sub.9                                      191 CH.sub.3                                                                           4-I   6-Cl  CH.sub.3                                                 192 CH.sub.3                                                                           4-Br  6-Cl  --CH.sub.2 --CH═CH.sub.2                             193 CH.sub.3                                                                           4-Br  6-C.sub.2 H.sub.5                                                                   --CH.sub.2 --CH═CH.sub.2                                                               b.p. 183°-185° C./0.02                                          Torr                                        194 CH.sub.3                                                                           4-Br  6-Cl  C.sub.2 H.sub.5                                          195 CH.sub.3                                                                           4-Br  6-Cl  sec.C.sub.4 H.sub.9                                      196 CH.sub.3                                                                           4-Br  6-C.sub.2 H.sub.5                                                                   C.sub.6 H.sub.5                                          197 CH.sub.3                                                                           4-Br  6-C.sub.6 H.sub.5                                                                   CH.sub.2 C.sub.6 H.sub.5                                 198 CH.sub.3                                                                           4-I   6-C.sub.2 H.sub.5                                                                   CH.sub.3     b.p. 192°-197° C./0.03                                          Torr                                        __________________________________________________________________________

The following compounds of the formula ##STR27## can also bemanufactured in analogous manner: (R₁ =2-position).

    __________________________________________________________________________                                                     Physical constant            Compound                                                                            R.sub.1                                                                             R.sub.2                                                                             R.sub.7                                                                            R.sub.8                                                                           XR.sub.3    Z.sub.2   (temperatures in                                                              °C.)                  __________________________________________________________________________    199   CH.sub.3                                                                            6-CH.sub.3                                                                          H    H                                                                                  ##STR28##  CH.sub.3  b.p. 136°-138.degr                                                     ee. C./0.02 Torr             200   CH.sub.3                                                                            6-CH.sub.3                                                                          H    H                                                                                  ##STR29##  isoC.sub.3 H.sub.7                     201   CH.sub.3                                                                            6-Cl  H    H                                                                                  ##STR30##  CH.sub.3                               202   Cl    6-Cl  H    H                                                                                  ##STR31##  CH.sub.3                               203   CH.sub.3                                                                            6-CH.sub.3                                                                          H    H                                                                                  ##STR32##  C.sub.6 H.sub.5                        204   CH.sub.3                                                                            6-CH.sub.3                                                                          H    H                                                                                  ##STR33##  CH.sub.2C.sub.6 H.sub.5                                                                 b.p. 178°-182.degr                                                     ee. C./0.03 Torr             205   Br    H     H    H                                                                                  ##STR34##  isoC.sub.3 H.sub.7                     206   CH.sub.3                                                                            6-CH.sub.3                                                                          H    H   CH.sub.2COOCH.sub.3                                                                       C.sub.2 H.sub.5                        207   CH.sub.3                                                                            6-CH.sub.3                                                                          H    H   CH.sub.2COOCH.sub.3                                                                       sec.C.sub.4 H.sub.9                                                                     b.p. 162°-165.degr                                                     ee. C./0.04 Torr             208   Cl    H     H    H   CH.sub.2COOCH.sub.3                                                                       isoC.sub.5 H.sub.11                    209   Cl    6-Cl  H    H   CH.sub.2COOCH.sub.3                                                                       isoC.sub.3 H.sub.7                     210   Cl    6-Cl  H    H   CH.sub.2COOCH.sub.3                                                                       CH.sub.3                               211   CH.sub.3                                                                            6-CH.sub.3                                                                          H    H   CH.sub.2COOCH.sub.3                                                                       C.sub.6 H.sub.5                                                                         m.p. 82°-85.degree                                                     . C.                         212   Cl    6-Cl  H    H   CH.sub.2COOCH.sub.3                                                                       C.sub.6 H.sub.3 Cl.sub.2 (2,4)         213   CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                   H    H   CH.sub.2COOCH.sub.3                                                                       C.sub.6 H.sub.5                                                                         m.p. 70°-74.degree                                                     . C.                         214   CH.sub.3                                                                            6-Cl  H    H   CH.sub.2COOCH.sub.3                                                                       C.sub.6 H.sub.5                        215   CH.sub.3                                                                            6-CH.sub.3                                                                          H    H    CH.sub.2COOCH.sub.3                                                                      C.sub.6 H.sub.3 Cl.sub.2 (2,4)                                                          m.p. 102°-105.degr                                                     ee. C.                       216   CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                   H    H   CH.sub.2COOCH.sub.3                                                                       C.sub.6 H.sub.3 Cl.sub.2 (2,4)                                                          m.p. 82°-84.degree                                                     . C.                         217   C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                   H    H   CH.sub.2COOCH.sub.3                                                                       C.sub.6 H.sub.3 Cl.sub.2 (2,4)                                                          m.p. 82°-85.degree                                                     . C.                         218   C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                   H    H   CH.sub.2COOCH.sub.3                                                                       CH.sub.3  m.p. 50°-52.degree                                                     . C.                         219   CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                   H    H   CH.sub.2COOCH.sub.3                                                                       isoC.sub.3 H.sub.7                     220   I     6-C.sub.2 H.sub.5                                                                   H    H   CH.sub.2COOCH.sub.3                                                                       CH.sub.3                               221   C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                   H    H   CH.sub.2COOCH.sub.3                                                                       C.sub.6 H.sub.5                        222   CH.sub.3                                                                            3-CH.sub.3                                                                          6-CH.sub.3                                                                         H   CH.sub.2COOCH.sub.3                                                                       CH.sub.3  oil                          223   CH.sub.3                                                                            4-CH.sub.3                                                                          6-CH.sub.3                                                                         H   CH.sub.2COOCH.sub.3                                                                       CH.sub.3                               224   CH.sub.3                                                                            3-CH.sub.3                                                                          5-CH.sub.3                                                                         6-CH.sub.3                                                                        CH.sub.2COOCH.sub.3                                                                       CH.sub.3                               225   CH.sub.3                                                                            4-Cl  6-CH.sub.3                                                                         H   CH.sub.2COOCH.sub.3                                                                       CH.sub.3                               226   CH.sub.3                                                                            6-CH.sub.3                                                                          H    H   CH.sub.2CONH.sub.2                                                                        CH.sub.3                               227   CH.sub.3                                                                            6-CH.sub.3                                                                          H    H   CH.sub.2CONHCH.sub.3                                                                      CH.sub.3                               228   CH.sub.3                                                                            6-CH.sub.3                                                                          H    H   CH.sub.2CONHCH.sub.3                                                                      C.sub.2 H.sub.5                        229   CH.sub.3                                                                            6-CH.sub.3                                                                          H    H   CH.sub.2CONHCH.sub.3                                                                      isoC.sub.3 H.sub.7                     230   CH.sub.3                                                                            6-Cl  H    H   CH.sub.2CONHCH.sub.3                                                                      CH.sub.3                               231   CH.sub.3                                                                            6-Cl  H    H   CH.sub.2CONHCH.sub.3                                                                      C.sub.2 H.sub.5                        232   Cl    6-Cl  H    H   CH.sub.2CONHCH.sub.3                                                                      C.sub.2 H.sub.5                        233   C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                   H    H   CH.sub.2CONHCH.sub.3                                                                      CH.sub.3                               234   C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                   H    H   CH.sub.2CONHCH.sub.3                                                                      isoC.sub.3 H.sub.7                                                                      m.p. 96° C.           235   C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                   H    H   CH.sub.2CONHC.sub.2 H.sub.5                                                               CH.sub.3  b.p. 165°-170.degr                                                     ee. C./0.3 Torr              236   CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                   H    H   CH.sub.2CONHCH.sub. 3                                                                     CH.sub.3                               237   CH.sub.3                                                                            6-CH.sub.3                                                                          H    H   CH.sub.2CONH.sub.2                                                                        CH.sub.2CHCH.sub.2                     238   CH.sub.3                                                                            6-CH.sub.3                                                                          H    H   CH.sub.2CONHCH.sub.3                                                                      CH.sub.2CHCH.sub.2                     239   CH.sub.3                                                                            6-Cl  H    H   CH.sub.2CONHC.sub.2 H.sub.5                                                               CH.sub.2CHCH.sub.2                     240   CH.sub.3                                                                            6-CH.sub.3                                                                          H    H   CH.sub.2CONHCH.sub.3                                                                      CH.sub.2CCH                            241   CH.sub.3 O                                                                          4-CH.sub.3 O                                                                        6-CH.sub.3 O                                                                       H   CH.sub.2CONHCH.sub.3                                                                      CH.sub.2CHCH.sub.2                     242   CH.sub.3 O                                                                          4-CH.sub.3 O                                                                        6-CH.sub.3 O                                                                       H   CH.sub.2CONHCH.sub.3                                                                      CH.sub.3                               243   CH.sub.3                                                                            4-CH.sub.3                                                                          6-CH.sub.3                                                                         H   CH.sub.2CONHCH.sub.3                                                                      CH.sub.2CHCH.sub.2                     244   C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                   H    H   CH.sub.2CONHCH.sub.3                                                                      CH.sub.2CHCH.sub.2                     245   C.sub.2 H.sub.5                                                                     6-Cl  H    H   CH.sub.2CONHCH.sub.3                                                                      CH.sub.2CHCH.sub.2                     246   C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                   H    H   CH.sub. 2CONH.sub.2                                                                       C.sub.6 H.sub.5                                                                         m.p. 147°-148.degr                                                     ee. C.                       247   C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                   H    H   CH.sub.2CONHCH.sub.3                                                                      C.sub.6 H.sub.5                                                                         m.p. 122°-124.degr                                                     ee. C.                       248   CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                   H    H   CH.sub.2CONHCH.sub.3                                                                      C.sub.6 H.sub.5                                                                         m.p. 108°-111.degr                                                     ee. C.                       249   CH.sub.3                                                                            6-CH.sub.3                                                                          H    H   CH.sub.2CONHCH.sub.3                                                                      C.sub.6 H.sub.5                                                                         m.p. 122°-124.degr                                                     ee. C.                       250   CH.sub.3                                                                            6-Cl  H    H   CH.sub.2CONHCH.sub.3                                                                      C.sub.6 H.sub.5                        251   Cl    6-Cl  H    H   CH.sub.2CONHCH.sub.3                                                                      C.sub.6 H.sub.5                        252   CH.sub.3                                                                            4-CH.sub.3                                                                          6-CH.sub.3                                                                         H   CH.sub.2CONHCH.sub.3                                                                      C.sub.6 H.sub.5                        253   C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                   H    H   CH.sub.2CONH.sub.2                                                                        C.sub.6 H.sub.3 Cl.sub.2 (2,4)                                                          m.p. 162°-164.degr                                                     ee. C.                       254   C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                   H    H   CH.sub.2CONHCH.sub.3                                                                      C.sub.6 H.sub.3 Cl.sub.2 (2,4)                                                          m.p. 167°-169.degr                                                     ee. C.                       255   C.sub. 2 H.sub.5                                                                    6-C.sub.2 H.sub.5                                                                   H    H   CH.sub.2CONHC.sub.2 H.sub.5                                                               C.sub.6 H.sub.3 Cl.sub.2 (2,4)                                                          m.p. 119°-121.degr                                                     ee. C.                       256   CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                   H    H   CH.sub.2CONHCH.sub.3                                                                      C.sub.6 H.sub.3 Cl.sub.2 (2,4)                                                          m.p. 137°-141.degr                                                     ee. C.                       257   CH.sub.3                                                                            6-CH.sub.3                                                                          H    H   CH.sub.2CONHCH.sub.3                                                                      C.sub.6 H.sub.3 Cl.sub.2 (2,4)                                                          m.p. 104°-107.degr                                                     ee. C.                       258   CH.sub.3                                                                            4-CH.sub.3                                                                          6-CH.sub.3                                                                         H   CH.sub.2CONHCH.sub.3                                                                      C.sub.6 H.sub.3 Cl.sub.2 (2,4)         __________________________________________________________________________

The following compounds of the formula ##STR35## can also bemanufactured in analogous manner: (R₁ =2-position).

    __________________________________________________________________________                                              Physical constant                   Compound                                                                            R.sub.1                                                                          R.sub.2                                                                           R.sub.7                                                                           R.sub.8                                                                           XR.sub.3    Z.sub.3  (temperatures in                    __________________________________________________________________________                                              °C.)                         259   CH.sub.3                                                                         6-CH.sub.3                                                                        H   H   CH(CH.sub.3)COOCH.sub.3                                                                   CH.sub.2C.sub.6 H.sub.5                                                                b.p. 190°-192°                                                  C./0.15 Torr                        260   CH.sub.3                                                                         6-C.sub.2 H.sub.5                                                                 H   H   CH(CH.sub.3)COOCH.sub.3                                                                   CH.sub.2C.sub.6 H.sub.5                                                                b.p. 194°-197°                                                  C./0.2 Torr                         261   CH.sub.3                                                                         6-Cl                                                                              H   H   CH(CH.sub.3)COOCH.sub.3                                                                   CH.sub.2C.sub.6 H.sub.5                                                                b.p. 215°-220°                                                  C./0.07 Torr                        262   Cl 6-Cl                                                                              H   H   CH(CH.sub.3)COOCH.sub.3                                                                   CH.sub.2C.sub.6 H.sub.5                      263   CH.sub.3                                                                         3-CH.sub.3                                                                        6-CH.sub.3                                                                        H   CH(CH.sub.3)COOCH.sub.3                                                                   CH.sub.2C.sub.6 H.sub.5                                                                b.p. 188°-190°                                                  C./0.04 Torr                        264   CH.sub.3                                                                         4-CH.sub.3                                                                        6-CH.sub.3                                                                        H   CH(CH.sub.3)COOCH.sub.3                                                                   CH.sub.2C.sub.6 H.sub.5                                                                b.p. 205°-210°                                                  C./0.03 Torr                        265   CH.sub.3                                                                         6-CH.sub.3                                                                        H   H   CH.sub.2COOCH.sub.3                                                                       CH.sub.2C.sub.6 H.sub.5                      266   C.sub.2 H.sub.5                                                                  6-C.sub.2 H.sub.5                                                                 H   H   CH.sub.2CONH.sub.2                                                                        CH.sub.2C.sub.6 H.sub.5                      267   CH.sub.3                                                                         6-CH.sub.3                                                                        H   H   CH.sub.2CONHCH.sub.3                                                                      CH.sub.2C.sub.6 H.sub.5                      268   C.sub.2 H.sub.5                                                                  6-C.sub.2 H.sub.5                                                                 H   H   CH.sub.2CONHC.sub.2 H.sub.5                                                               CH.sub.2C.sub.6 H.sub.5                      269   CH.sub.3                                                                         6-Cl                                                                              H   H   CH.sub.2CONHCH.sub.3                                                                      CH.sub.2C.sub.6 H.sub.5                      270   C.sub.2 H.sub.5                                                                  6-C.sub.2 H.sub.5                                                                 H   H   CH.sub.2CONHCH.sub.3                                                                      CH.sub.2C.sub.6 H.sub.5                      271   CH.sub.3                                                                         6-CH.sub.3                                                                        H   H   CH(CH.sub.3)CONHCH.sub.3                                                                  CH.sub.2C.sub.6 H.sub.5                      272   CH.sub.3                                                                         6-CH.sub.3                                                                        H   H   CH(CH.sub.3)COOCH.sub.3                                                                    ##STR36##                                                                             b.p. 185°-195°                                                  C./0.1 Torr                         273   CH.sub.3                                                                         6-C.sub.2 H.sub.5                                                                 H   H   CH.sub.2COOCH.sub.3                                                                        ##STR37##                                                                             b.p. 187°-190°                                                  C./0.2 Torr                         274   C.sub.2 H.sub.5                                                                  6-C.sub.2 H.sub.5                                                                 H   H   CH.sub.2CONHCH.sub.3                                                                       ##STR38##                                                                             m.p. 70°-72° C.       275   C.sub.2 H.sub.5                                                                  6-C.sub.2 H.sub.5                                                                 H   H   CH.sub.2CONH.sub.2                                                                         ##STR39##                                                                             m.p. 83°-86° C.       276   CH.sub.3                                                                         3-CH.sub.3                                                                        6-CH.sub.3                                                                        H   CH(CH.sub.3)COOCH.sub.3                                                                    ##STR40##                                   277   CH.sub.3                                                                         3-CH.sub.3                                                                        6-CH.sub.3                                                                        H   CH(CH.sub.3)COOCH.sub.3                                                                   CH.sub.3                                     278   CH.sub.3                                                                         3-CH.sub.3                                                                        6-CH.sub.3                                                                        H   CH(CH.sub.3)COOCH.sub.3                                                                   C.sub.2 H.sub.5                              279   CH.sub.3                                                                         3-CH.sub.3                                                                        6-CH.sub.3                                                                        H   CH(CH.sub.3)COOCH.sub.3                                                                   isoC.sub.3 H.sub.7                           280   CH.sub.3                                                                         4-CH.sub.3                                                                        6-CH.sub.3                                                                        H   CH(CH.sub.3)COOCH.sub.3                                                                   CH.sub.3                                     281   CH.sub.3                                                                         4-CH.sub.4                                                                        6-CH.sub.3                                                                        H   CH(CH.sub.3)COOCH.sub.3                                                                   isoC.sub.3 H.sub.7                                                                     b.p. 151°-153°                                                  C./0.15 Torr                        282   CH.sub. 3                                                                        3-CH.sub.3                                                                        5-CH.sub.3                                                                        6-CH.sub.3                                                                        CH(CH.sub.3)COOCH.sub.3                                                                   CH.sub.3                                     283   CH.sub.3                                                                         5-CH.sub.3                                                                        6-C.sub.2 H.sub.5                                                                 H   CH(CH.sub.3)COOCH.sub.3                                                                   CH.sub.3 b.p. 134°-136°                                                  10.02 Torr                          284   CH.sub.3                                                                         5-CH.sub.3                                                                        6-C.sub.2 H.sub.5                                                                 H   CH(CH.sub.3)COOCH.sub.3                                                                   C.sub.2 H.sub.5                              285   CH.sub.3                                                                         3-Br                                                                              6-CH.sub.3                                                                        H   CH(CH.sub.3)COOCH.sub.3                                                                   CH.sub.3 b.p. 180°-182°                                                  C./0.06 Torr                        286   CH.sub.3                                                                         4-CH.sub.3                                                                        6-CH.sub.3                                                                        H   CH(CH.sub.3)COOCH.sub.3                                                                   C.sub.6 H.sub.4CH.sub.3 (4)                                                            m.p. 98°-99° C.       287   CH.sub.3                                                                         4-CH.sub.3                                                                        6-CH.sub.3                                                                        H   CH(CH.sub.3)COOCH.sub.3                                                                   C.sub.6 H.sub.5                                                                        m.p. 63.5°-64.5°                                                C.                                  288   CH.sub.3                                                                         4-CH.sub.3                                                                        6-CH.sub.3                                                                        H   CH(CH.sub.3)COOCH.sub.3                                                                   C.sub.6 H.sub.4 Cl(4)                                                                  m.p. 71°-72.5°                                                  C.                                  289   CH.sub.3                                                                         3-CH.sub.3                                                                        6-CH.sub.3                                                                        H   CH(CH.sub.3)COOCH.sub.3                                                                   C.sub.6 H.sub.5                              290   CH.sub.3                                                                         4-CH.sub.3                                                                        6-CH.sub.3                                                                        H   CH(CH.sub.3)COOCH.sub.3                                                                   CSN(CH.sub.3).sub.2                                                                    m.p. 146°-147°                                                  C.                                  291   CH.sub.3                                                                         4-CH.sub.3                                                                        6-CH.sub.3                                                                        H   CH(CH.sub.3)COOCH.sub.3                                                                    ##STR41##                                                                             m.p. 248°-250°                                                  (decomp.)                           292   CH.sub.3                                                                         3-CH.sub.3                                                                        6-CH.sub.3                                                                        H   CH(CH.sub.3)COOCH.sub.3                                                                    ##STR42##                                   293   CH.sub.3                                                                         3-CH.sub.3                                                                        6-CH.sub.3                                                                        H   CH(CH.sub.3)COOCH.sub.3                                                                   CSN(CH.sub.3).sub.2                          294   CH.sub.3                                                                         3-CH.sub.3                                                                        6-C.sub.2 H.sub.5                                                                 H   CH(CH.sub.3)COOCH.sub.3                                                                   CH.sub.3 m.p. 81°-92° C.       295   CH.sub.3                                                                         4-CH.sub.3                                                                        6-CH.sub.3                                                                        H   CH(CH.sub.3)COOCH.sub.3                                                                   C.sub.2 H.sub.5                                                                        m.p. 43°-45.5°                                                  C.                                  296   CH.sub.3                                                                         4-Cl                                                                              6-CH.sub.3                                                                        H   CH(CH.sub.3)COOCH.sub.3                                                                   C.sub.2 H.sub.5                              297   CH.sub.3                                                                         4-Cl                                                                              6-CH.sub.3                                                                        H   CH(CH.sub.3)COOCH.sub.3                                                                   CH.sub.3                                     298   CH.sub.3                                                                         4-Cl                                                                              6-CH.sub.3                                                                        H   CH(CH.sub.3)COOCH.sub.3                                                                   isoC.sub.3 H.sub.7                           299   CH.sub.3                                                                         4-Cl                                                                              6-CH.sub.3                                                                        H   CH(CH.sub.3)COOCH.sub.3                                                                   sec.C.sub.4 H.sub.9                          300   CH.sub.3                                                                         4-Br                                                                              6-CH.sub.3                                                                        H   CH(CH.sub.3)COOCH.sub.3                                                                   C.sub.2 H.sub.5                                                                        b.p. 175°-178°                                                  C./0.02 Torr                        301   CH.sub.3                                                                         4-Br                                                                              6-CH.sub.3                                                                        H   CH(CH.sub.3)COOCH.sub.3                                                                   nC.sub.4 H.sub.9                             302   CH.sub.3                                                                         4-Cl                                                                              6-CH.sub.3                                                                        H   CH(CH.sub.3)COOCH.sub.3                                                                   C.sub.6 H.sub.5                              303   CH.sub.3                                                                         4-Cl                                                                              6-CH.sub.3                                                                        H   CH(CH.sub.3)COOCH.sub.3                                                                   CH.sub.2 C.sub.6 H.sub.5                     304   CH.sub.3                                                                         4-Br                                                                              6-CH.sub.3                                                                        H   CH(CH.sub.3)COOCH.sub.3                                                                   iso-C.sub.3 H.sub.7                                                                    b.p. 180°-184°                                                  C./0.03 Torr                        305   CH.sub.3                                                                         3-CH.sub.3                                                                        6-CH.sub.3                                                                        H   CH(CH.sub.3)COOCH.sub.3                                                                   C.sub.6 H.sub.4 CH.sub.3 (4)                                                           b.p. 201°-203°                                                  C./0.04 Torr                        306   CH.sub.3                                                                         4-Cl                                                                              6-C.sub.2 H.sub.5                                                                 H   CH(CH.sub.3)COOCH.sub.3                                                                    ##STR43##                                   307   CH.sub.3                                                                         4-Cl                                                                              6-C.sub.2 H.sub.5                                                                 H   CH(CH.sub.3)COOCH.sub.3                                                                   C.sub.2 H.sub.5                              308   CH.sub.3                                                                         4-Cl                                                                              6-C.sub.2 H.sub.5                                                                 H   CH(CH.sub.3)COOCH.sub.3                                                                   CH.sub.3                                     309   CH.sub.3                                                                         4-Cl                                                                              6-C.sub.2 H.sub.5                                                                 H   CH(CH.sub.3)COOCH.sub.3                                                                   C.sub.2 H.sub.5                              310   CH.sub.3                                                                         4-Cl                                                                              6-CH.sub.3                                                                        H   CH(CH.sub.3)COOCH.sub.3                                                                   C.sub.6 H.sub.4 tert.-C.sub.4 H.sub.9                                         (4)                                          311   CH.sub.3                                                                         4-Br                                                                              6-CH.sub.3                                                                        H   CH(CH.sub.3)COOCH.sub.3                                                                   C.sub.6 H.sub.5                              312   CH.sub.3                                                                         4-Br                                                                              6-CH.sub.3                                                                        H   CH(CH.sub.3)COOCH.sub.3                                                                   sec.C.sub.4 H.sub.9                          313   CH.sub.3                                                                         4-Br                                                                              6-CH.sub.3                                                                        H   CH(CH.sub.3)COOCH.sub.3                                                                   CH.sub.2 C.sub.6 H.sub.5                                                               brown oil                           314   CH.sub.3                                                                         4-Cl                                                                              6-C.sub.2 H.sub.5                                                                 H   CH(CH.sub.3)COOCH.sub.3                                                                   sec.C.sub.4 H.sub.9                          315   CH.sub.3                                                                         4-Cl                                                                              6-C.sub.2 H.sub.5                                                                 H   CH(CH.sub.3)COOCH.sub.3                                                                   iso C.sub.3 H.sub.7                          316   CH.sub.3                                                                         4-Br                                                                              6-C.sub.2 H.sub.5                                                                 H   CH(CH.sub.3)COOCH.sub.3                                                                   C.sub.2 H.sub.5                              317   CH.sub.3                                                                         4-I 6-CH.sub.3                                                                        H   CH(CH.sub.3)COOCH.sub.3                                                                   C.sub.2 H.sub.5                                                                        m.p. 105°-107°                                                  C.                                  318   CH.sub.3                                                                         4-I 6-CH.sub.3                                                                        H   CH(CH.sub.3)COOCH.sub.3                                                                   iso C.sub.3 H.sub.7                          319   CH.sub.3                                                                         4-Cl                                                                              6-Cl                                                                              H   CH(CH.sub.3)COOCH.sub.3                                                                   C.sub.2 H.sub.5                              320   CH.sub.3                                                                         4-Cl                                                                              6-Cl                                                                              H   CH(CH.sub.3)COOCH.sub.3                                                                   sec.C.sub.4 H.sub.9                          321   CH.sub.3                                                                         4-Cl                                                                              6-Cl                                                                              H   CH(CH.sub.3)COOCH.sub.3                                                                   C.sub.6 H.sub.5                              322   CH.sub.3                                                                         4-Br                                                                              6-Cl                                                                              H   CH(CH.sub.3)COOCH.sub.3                                                                   C.sub.2 H.sub.5                              323   CH.sub.3                                                                         4-Br                                                                              6-Cl                                                                              H   CH(CH.sub.3)COOCH.sub.3                                                                   CH.sub.3                                     324   CH.sub.3                                                                         4-Br                                                                              6-Cl                                                                              H   CH(CH.sub.3)COOCH.sub.3                                                                   C.sub.6 H.sub.5                              325   CH.sub.3                                                                         4-Br                                                                              6-CH.sub.3                                                                        H   CH(CH.sub.3)COOCH.sub.3                                                                   C.sub.6 H.sub.4CH.sub.3 (4)                                                            m.p. 87°-91° C.       326   CH.sub.3                                                                         4-Br                                                                              6-CH.sub.3                                                                        H   CH(CH.sub.3)COOCH.sub.3                                                                    ##STR44##                                   327   CH.sub.3                                                                         4-Br                                                                              6-CH.sub.3                                                                        H   CH(CH.sub.3)COOCH.sub.3                                                                    ##STR45##                                                                             m.p. 257°-260°        __________________________________________________________________________                                              C.                              

The following compounds of the formula ##STR46## can also bemanufactured in analogous manner: (R₁ =2-position).

    __________________________________________________________________________    Com-                                      Physical constant                   pound                                                                             R.sub.1                                                                             R.sub.2                                                                           XR.sub.3     Y              (temperatures in                    __________________________________________________________________________                                              °C.)                         328 CH.sub.3                                                                            6-CH.sub.3                                                                        CH(CH.sub.3)COOCH.sub.3                                                                    SCH.sub.3      m.p. 65°-67° C.       329 CH.sub.3                                                                            6-CH.sub.3                                                                        CH(CH.sub.3)COOCH.sub.3                                                                    SC.sub.2 H.sub.5                                                                             m.p. 55.5°-56°                                                  C.                                  330 CH.sub.3                                                                            6-CH.sub.3                                                                        CH(CH.sub.3)COOCH.sub.3                                                                    SnC.sub.3 H.sub.7                                                                            b.p. 166°-169°                                                  C./0.04 Torr                        331 CH.sub.3                                                                            6-CH.sub.3                                                                        CH(CH.sub.3)COOCH.sub.3                                                                    SisoC.sub.3 H.sub.7                                                                          b.p. 145°-148°                                                  C./0.02 Torr                        332 CH.sub.3                                                                            6-Cl                                                                              CH(CH.sub.3)COOCH.sub.3                                                                    SCH.sub.3                                          333 CH.sub.3                                                                            6-Cl                                                                              CH(CH.sub.3)COOCH.sub.3                                                                    SisoC.sub.3 H.sub.7                                                                          m.p. 81°-95° C.       334 CH.sub.3                                                                            6-Cl                                                                              CH(CH.sub.3)COOCH.sub.3                                                                    Ssec.C.sub.4 H.sub.9                                                                         b.p. 154°-156°                                                  C./0.09 Torr                        335 Cl    6-Cl                                                                              CH(CH.sub.3)COOCH.sub.3                                                                    SCH.sub.3                                          336 Cl    6-Cl                                                                              CH(CH.sub.3)COOCH.sub.3                                                                    SC.sub.2 H.sub.5                                   337 CH.sub.3                                                                            6-CH.sub.3                                                                        CH(CH.sub.3)COOCH.sub.3                                                                    Ssec.C.sub.4 H.sub.9                                                                         b.p. 172°-174°                                                  C./0.1 Torr                         338 CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                 CH(CH.sub.3)COOCH.sub.3                                                                    SCH.sub.3                                          339 CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                 CH(CH.sub.3)COOCH.sub.3                                                                    SC.sub.2 H.sub.5                                                                             b.p. 162°-164°                                                  C./0.1 Torr                         340 CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                 CH(CH.sub.3)COOCH.sub.3                                                                    SisoC.sub.3 H.sub.7                                                                          b.p. 152°-155°                                                  C./0.06 Torr                        341 C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                 CH(CH.sub.3)COOCH.sub.3                                                                    SCH.sub.3                                          342 CH.sub.3                                                                            6-CH.sub.3                                                                        CH(CH.sub.3)COOCH.sub.3                                                                    SCH.sub.2CHCH.sub.2                                343 CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                 CH(CH.sub.3)COOCH.sub.3                                                                    SnC.sub.4 H.sub.9                                                                            b.p. 197°-199°                                                  C./0.02 Torr                        344 CH.sub.3                                                                            6-CH.sub.3                                                                        CH(CH.sub.3)COOCH.sub.3                                                                    SCH.sub.2 CHCHCH.sub.3                             345 CH.sub.3                                                                            6-Cl                                                                              CH(CH.sub.3)COOCH.sub.3                                                                     SCH.sub.2 CHCHCH.sub.3                            346 CH.sub.3                                                                            6-CH.sub.3                                                                        CH(CH.sub.3)COOCH.sub.3                                                                    SCH.sub.2 CCH                                      347 CH.sub.3                                                                            6-Cl                                                                              CH(CH.sub.3)COOCH.sub.3                                                                    SCH.sub.2 CCH                                      348 CH.sub.3                                                                            6-Cl                                                                              CH(CH.sub.3)COOCH.sub.3                                                                    SCH.sub.2 CCI                                      349 CH.sub.3                                                                            6-CH.sub.3                                                                        CH(CH.sub.3)COOCH.sub.3                                                                    SnC.sub.4 H.sub.9                                                                            b.p. 172°-174°                                                  C./0.1 Torr                         350 CH.sub.3                                                                            6-CH.sub.3                                                                        CH(CH.sub.3)COOCH.sub.3                                                                    SC.sub.6 H.sub.5                                                                             b.p. 178°-179°                                                  C./0.08 Torr                        351 CH.sub.3                                                                            6-Cl                                                                              CH(CH.sub.3)COOCH.sub.3                                                                    SC.sub.6 H.sub.5                                                                             m.p. 83°-85° C.       352 CH.sub.3                                                                            6-CH.sub.3                                                                        CH(CH.sub.3)COOCH.sub.3                                                                    SC.sub.6 H.sub.4 Cl(4)                                                                       m.p. 63°-64° C.       353 Cl    6-Cl                                                                              CH(CH.sub.3)COOCH.sub.3                                                                    SC.sub.6 H.sub.4 Cl(4)                             354 CH.sub.3                                                                            6-Cl                                                                               CH(CH.sub.3)COOCH.sub.3                                                                    ##STR47##     b.p. 210°-212°                                                  C./0.02 Torr                        355 Cl    6-Cl                                                                              CH(CH.sub.3)COOCH.sub.3                                                                     ##STR48##                                         356 CH.sub.3                                                                            6-CH.sub.3                                                                        CH(CH.sub.3)COOCH.sub.3                                                                     ##STR49##     b.p. 197°-199°                                                  C./0.09 Torr                        357 C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                 CH.sub.2 COOCH.sub.3                                                                       SCH.sub.3      b.p. 158°-160°                                                  C./0.05 Torr                        358 CH.sub.3                                                                            6-CH.sub.3                                                                        CH.sub.2COOCH.sub.3                                                                        SCH.sub.3                                          359 CH.sub.3                                                                            6-Cl                                                                              CH.sub.2 COOCH.sub.3                                                                       SCH.sub.2 CHCH.sub.2                               360 CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                 CH(CH.sub.3)COOCH.sub. 3                                                                   SC.sub.6 H.sub.4 CH.sub.3 (4)                                                                b.p. 210°-212°                                                  C./0.08 Torr                        361 Cl    4-Cl                                                                              CH(CH.sub.3)CONH.sub.2                                                                      ##STR50##                                         362 nC.sub.3 H.sub.7 O                                                                  H   CH.sub.2 CONH.sub.2                                                                        SC.sub.6 H.sub.5                                   363 CH.sub.3                                                                            6-CH.sub.3                                                                        CH.sub.2 CONH.sub.2                                                                        SCH.sub.3                                          364 CH.sub.3                                                                            6-Cl                                                                              CH(CH.sub.3)CON(C.sub.2 H.sub.5).sub.2                                                     SC.sub.2 H.sub.5                                   365 CH.sub.3                                                                            6-CH.sub.3                                                                        CH.sub.2 CONHCH.sub.3                                                                      SCH.sub.3                                          366 C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                 CH.sub.2 CONHCH.sub.3                                                                      SCH.sub.3                                          367 C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                 CH.sub.2 CONHC.sub.2 H.sub.5                                                               SCH.sub.3      b.p. 151°-175°                                                  C./0.1 Torr                         368 CH.sub.3                                                                            6-CH.sub.3                                                                        CH.sub.2 CONHCH.sub.3                                                                      SC.sub.6 H.sub.4 CH.sub.3 (4)                      369 C.sub.2 H.sub.5 O                                                                   H   CH.sub.2 CON(CH.sub.3).sub.2                                                               SisoC.sub.3 H.sub.7                                370 CH.sub.3                                                                            6-CH.sub.3                                                                        CH(CH.sub.3)COOC.sub.2 H.sub.5                                                             SC(CH.sub.3).sub.3                                 371 CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                 CH(CH.sub.3)COOC.sub.2 H.sub.5                                                             SC(CH.sub.3 ).sub.3                                372 Cl    5-Cl                                                                              CH(CH.sub.3)COOC.sub.2 H.sub.5                                                             SCH.sub.3                                          373 C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                 CH.sub.2 COOC.sub.2 H.sub.5                                                                SCH.sub.3                                          374 CH.sub.3                                                                            6-CH.sub.3                                                                        CH(CH.sub.3)COOCH.sub.3                                                                    SCSN(CH.sub.3).sub.2                                                                         m.p. 127°-128.5°                                                C.                                  375 CH.sub.3                                                                            6-CH.sub.3                                                                        CH.sub.2 CONH.sub.2                                                                        SCSN(nC.sub.3 H.sub.7).sub.2                       376 CH.sub.3                                                                            4-CH.sub.3                                                                        CH(CH.sub.3)COOCH.sub.3                                                                    SCSN(CH.sub.3).sub.2                                                                         m.p. 95°-96° C.       377 CH.sub.3                                                                            5-CH.sub.3                                                                        CH(CH.sub.3)COOCH.sub.3                                                                    SCSN(CH.sub.3).sub.2                                                                         m.p. 98°-99° C.       378 CH.sub.3                                                                            6-CH.sub.3                                                                        CH(CH.sub.3)COOCH.sub.3                                                                     ##STR51##     m.p. 258°-260°                                                  C.                                  379 CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                 CH(CH.sub.3)COOCH.sub.3                                                                     ##STR52##     m.p. 228°-230°                                                  C.                                  380 C.sub.2 H.sub.5                                                                     6-C.sub.2 H.sub.5                                                                 CH(CH.sub.3)COOCH.sub. 3                                                                    ##STR53##     m.p. 230°-232°                                                  C.                                  381 Cl    5-Cl                                                                              CH(CH.sub.3)COOCH.sub.3                                                                     ##STR54##                                         382 CH.sub.3                                                                            4-CH.sub.3                                                                        CH(CH.sub.3)COOCH.sub.3                                                                     ##STR55##     m.p. 217°-218°                                                  C.                                  383 CH.sub.3                                                                            5-CH.sub.3                                                                        CH(CH.sub.3)COOCH.sub.3                                                                     ##STR56##     m.p. 215°-216°                                                  C.                                  384 Cl    5-Cl                                                                              CH(CH.sub.3)COOCH.sub.3                                                                     ##STR57##     m.p. 219°-220°                                                  C.                                  385 CH.sub.3                                                                            6-CH.sub.3                                                                        CH(CH.sub.3)COOCH.sub.3                                                                    Stert.C.sub.4 H.sub.9                                                                        b.p. 145°-147°                                                  C./0.03 Torr                        386 CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                 CH(CH.sub.3)COOCH.sub.3                                                                    SC.sub.6 H.sub.5                                                                             b.p. 191°-193°                                                  C./0.2 Torr                         387 CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                 CH(CH.sub.3)COOCH.sub.3                                                                    SC.sub.6 H.sub.4 Cl(4)                                                                       m.p. 52°-55° C.       388 CH.sub.3                                                                            6-Cl                                                                              CH(CH.sub.3)COOCH.sub.3                                                                    SC.sub.6 H.sub.4 CH.sub.3 (4)                                                                b.p. 202°-205°                                                  C./0.2 Torr                         389 CH.sub.3                                                                            6-Cl                                                                              CH(CH.sub.3)COOCH.sub.3                                                                    SnC.sub.4 H.sub.9                                                                            m.p. 51°-56° C.       390 CH.sub.3                                                                            6-Cl                                                                              CH(CH.sub.3)COOCH.sub.3                                                                    SC.sub.2 H.sub.5                                                                             b.p. 166°-168°                                                  C./0.08 Torr                        391 CH.sub.3                                                                            6-Cl                                                                              CH(CH.sub.3)COOCH.sub.3                                                                    Stert.C.sub.4 H.sub.9                                                                        b.p. 138°-141°                                                  C./0.08 Torr                        392 CH.sub.3                                                                            6-C.sub.2 H.sub.5                                                                 CH(CH.sub.3)COOCH.sub.3                                                                    Ssec.C.sub.4 H.sub.9                                                                         b.p. 171°-173°                                                  C./0.1 Torr                         393 CH.sub.3                                                                            6-Cl                                                                              CH(CH.sub.3)COOCH.sub.3                                                                    SC.sub.6 H.sub.4 Cl(4)                                                                       m.p. 77°-79°          __________________________________________________________________________                                              C.                              

The compounds of the formula I can be used with other suitablepesticides or active substances that promote plant growth in order towiden their activity spectrum. The compounds of the formula I can beused by themselves or together with suitable carriers and/or otheradditives. Suitable carriers and additives can be solid or liquid andcorrespond to the customary substances used in formulation technology,for example natural or regenerated mineral substances, solvents,dispersants, wetting agents, stickers, thickeners, binders orfertilisers. The amount of active substance in commercially usefulcompositions is between 0.1 and 90%.

The compounds of the formula I can be applied in the following processforms (the percentages by weight in brackets denote the advantageousamounts of active substances):

solid forms: dusts and tracking agents (up to 10%); granules; coatedgranules impregnated granules and homogeneous granules (1 to 80%);

liquid forms:

(a) active substance concentrates which are dispersible in water:wettable powders and pastes (25-90% in the commercial pack, 0.01 to 15%in ready for use solution);

emulsion concentrates and concentrated solutions (10 to 50%; 0.01 to 15%in ready for use solution);

(b) solutions (0.1 to 20%).

The active substances of the formula I can be formulated, for example,as follows:

Dusts: The following substances are used to manufacture (a) 5% and (b) a2% dust:

    ______________________________________                                        (a)        5     parts of active substance                                               95    parts of talcum;                                             (b)        2     parts of active substance                                               1     part of highly disperse silicic acid                                    97    parts of talcum.                                             ______________________________________                                    

The active substances are mixed with the carriers and ground and in thisform can be processed to dusts for application.

Granules: The following substances are used to manufacture 5% granules:

5 parts of active substances

0.25 parts of epichlorohydrin

0.25 parts of cetyl polyglycol ether

3.50 parts of polyethylene glycol

91 parts of kaolin (particle size 0.3-0.8 mm).

The active substance is mixed with epichlorohydrin and the mixture isdissolved in 6 parts of acetone. Then polyethylene glycol and cetylpolyglycol ether are added. The resultant solution is sprayed on kaolinand the acetone is evaporated in vacuo. Such microgranules areadvantageously used for combating soil fungi.

Wettable powders: The following constituents are used to manufacture (a)a 70%, (b) a 40%, (c) and (d) a 25% and (e) a 10% wettable powder:

    ______________________________________                                        (a) 70     parts of active substance                                              5      parts of sodium dibutyl naphthylsulphonate                             3      parts of naphthalenesulphonic acid/phenolsulphonic                            acid/formaldehyde condensate (3:2:1)                                   10     parts of kaolin                                                        12     parts of Champagne chalk                                           (b) 40     parts of active substance                                              5      parts of sodium lignin sulphonate                                      1      part of sodium dibutylnaphthalenesulphonic acid                        54     parts of silicic acid                                              (c) 25     parts of active substance                                              4.5    parts of calcium lignin sulphonate                                     1.9    parts of Champagne chalk/hydroxyethyl cellulose                               mixture (1:1)                                                          1.5    parts of sodium dibutylnaphthalenesulphonate                           19.5   parts of silicic acid                                                  19.5   parts of Champagne chalk                                               28.1   parts of kaolin                                                    (d) 25     parts of active substance                                              2.5    parts of isooctylphenoxy-polyethylene-ethanol                          1.7    parts of a Champagne chalk/hydroxyethyl cellulose                             mixture (1:1)                                                          8.3    parts of sodium aluminium silicate                                     16.3   parts of kieselguhr                                                    46     parts of kaolin                                                    (e) 10     parts of active substance                                              3      parts of a mixture of the sodium salts of saturated                           fatty alcohol sulphates                                                5      parts of naphthalenesulphonic acid/formaldehyde                               condensate                                                             82     parts of kaolin.                                                   ______________________________________                                    

The active substances are intimately mixed in suitable mixers with theadditives and ground in appropriate mills and rollers. Wettable powdersof excellent wettability and suspension powder are obtained. Thesewettable powders can be diluted with water to give suspensions of everydesired concentration and can be used in particular for application toleaves.

Emulsifiable concentrates: The following substances are used tomanufacture a 25% emulsifiable concentrate:

25 parts of active substance

2.5 parts of epoxidised vegetable oil

10 parts of an alkylarylsulphonate/fatty alcohol polyglycol ethermixture

5 parts of dimethyl formamide

57.5 parts of xylene.

By diluting such concentrates with water it is possible to manufactureemulsions of every desired concentration which are especially suitablefor application to leaves.

EXAMPLE 4 Action against Phytophthora infestans on Solanum lycopersicum(tomatoes)

(Ia) Residual preventive action

Solanum lycopersicum plants of the "Roter Gnom" variety are infectedwhen 3 weeks old with a zoospore suspension of Phytophthora infestansafter they have been sprayed with a broth prepared from the activesubstance processed to a wetable powder and containing 0.05% of activesubstance, and dried. They are then kept for 6 days in a climaticchamber at 18° to 20° and high humidity, which is produced with anartificial wet fog. After this time typical leaf specks appear. Theirnumber and size are the criterion for evaluating the tested substance.

(Ib) Curative action:

"Rotor Gnom" tomato plants are sprayed when 3 weeks old with a zoosporesuspension of the fungus and incubated in a climatic chamber at 18° to20° C. and saturated humidity. The humidifying is interrupted after 24hours. After the plants have dried, they are sprayed with a broth whichcontains the active substance formulated as wettable powder in aconcentration of 0.05%. After the spray coating has dried, the plantsare again kept in the humid chamber for 4 days. Size and number of thetypical leaf specks which have occured during this time are thecriterion for evaluating the effectiveness of the tested substances.

(II) Preventive-systemic action

The active substance is applied as wettable powder in a concentration of0.05% (referred to the volume of the soil) to the surface of the soil of3 weeks old "Rotor Gnom" tomatoes in pots. Three days later theunderside of the leaves of the plants are sprayed with a zoosporesuspension of Phytophthora infestans. The plants are then kept for 5days in a spray chamber at 18° to 20° C. and saturated humidity, afterwhich time typical leaf specks form. The size and number of the specksserve as criterion for evaluating the effectiveness of the testedsubstance.

In these three tests, the compounds of the formula I effect a pronouncedleaf-fungicidal action. A fungus infection of less than 20% (averagevalues) is observed on application of the compounds of the subgroup Iain which R'=methyl. The fungus infection is almost completely inhibited(0-5%) with compounds 1, 2, 4, 5, 11, 18, 24, 28, 29, 33, 39, 118, 374,378 and others. A fungus infection of less than 20% (average values) isobserved when compounds 7, 9, 12, 16, 20, 30, 31, 32, 35, 36, 38, 44,65, 97, 98, 120, 130, 155, 157, 158, 159, 168, 199, 204, 222, 259, 272,281, 328, 331, 337, 350 and others are applied in an active substanceconcentration of only 0.02%.

EXAMPLE 5 Action against Plasmopara viticola (Bert. et Curt.) (Berl. etde Toni) on vines

(a) Residual preventive action

Vine cuttings of the variety "Chasselas" were reared in a greenhouse.Three plants in the 10 leaf stage were sprayed with a broth preparedfrom the active substance and formulated as a wettable powder. After thecoating layer had dried, the plants were infected on the underside ofthe leaves with the spore suspension of the fungus. The plants weresubsequently kept for 8 days in a humid chamber, after which timesymptoms of the disease were visible on the control plants. The numberand size of the infected areas on the treated plants served as criterionfor evaluating the effectiveness of the tested active substances.

(b) Curative action

Vine cuttings of the variety "Chasselas" were reared in a greenhouse andinfected in the 10 leaf stage with a spore suspension of Plasmoparaviticola on the underside of the leaves. After they had been kept for 24hours in a humid chamber, the plants were sprayed with an activesubstance broth prepared from a wettable powder of the active substance.

The plants were then kept for a further 7 days in a humid chamber, afterwhich time the symptoms of the disease were visible on the controlplants. The size and number of the infected areas served as criterionfor evaluating the effectiveness of the tested substances.

In both these tests the compounds of the formula I effected a pronouncedfungicidal action. Without exception the fungus infection was reduced toless than 20% with the compounds cited in Example 4. Almost no infection(0-5%) occured after application with a number of compounds, e.g.compounds, 1, 2, 4, 5, 18, 28, 29, 30, 33, 118.

EXAMPLE 6 Action against Erisyphe graminis on Hordeum vulgare (barley)

Residual protective action

Barley plants c. 8 cm in height were sprayed with a spray broth (0.05%active substance) prepared from a wettable powder of the activesubstance. After 48 hours the treated plants were dusted with conidia ofthe fungus. The infected barley plants were stood in a greenhouse at a.22° C. and the fungus infection was evaluated after 10 days. A number ofthe compounds of the formula I, effect in this test a reduction of thefungus infection to <20%.

EXAMPLE 7 Action against Pythium debaryanum in Beta vulgaris (sugarbeet)

(a) Action after soil application

The fungus is cultivated on sterile oat grains and added to a mixture ofearth and sand. Flower pots are filled with the infected soil in whichsugar beet seeds are then sown. Immediately after sowing, the testpreparations formulated as wettable powders are poured in the form ofaqueous suspensions over the soil (20 ppm of active substance referredto the volume of the soil). The pots are then stood for 2-3 weeks in agreenhouse at 20°-24° C. The soil is kept uniformly moist by gentlyspraying it with water. The emergence of the sugar beet plants as wellas the number of healthy and sick plants are ascertained in evaluatingthe tests.

(b) Action after seed dressing application

The fungus is cultivated on sterile oat grains and added to a mixture ofearth and sand. Flower pots are filled with the infected soil and sugarbeet seeds which have been treated with the test preparations formulatedas seed dressing powders are sown therein (1000 ppm of active substancereferred to the weight of the seeds). The pots are then stood in agreenhouse for 2-3 weeks at 20°-24° C. The soil is kept uniformly moistby gently spraying it with water. The emergence of the sugar beet plantsas well as the number of healthy and sick plants are ascertained. Underthe conditions of both test (a) and test (b), more than 85% of the sugarbeet plants emerged after treatment with one of the active substance ofthe formula I and had a healthy appearance. Less than 20% of the controlplants emerged and had in part a sickly appearance.

EXAMPLE 8 Growth inhibition of grasses

On a prepared outdoor lawn consisting of the grasses Lolium perenne, Poapratensis and Festuca rubra, parcels measuring 3 m² were sprayed 2 daysafter the first cutting in spring with aqueous preparations of an activesubstance of the formula I. The amount of active substance usedcorresponded to a rate of application of 5 kg per hectare. Untreatedparcels were left as controls. The average growth in height of thegrasses in treated and untreated parcels was ascertained 6 weeks afterthe application. The turf treated with the active substances wasuniformly compact and had a healthy appearance. Active substances of theformula I especially, where --X--R₃ represents the radical--CO--N(R")(R'") and Y represents --S--R₄ defined for the formula I,effected a pronounced growth inhibition.

I claim:
 1. A compound of the formula ##STR58## wherein R₂ representsmethyl, ethyl or chlorine,each of R₇ and R₈ independently representshydrogen or methyl, and Y represents --OR₄ or --SR₄ in which R₄represents methyl, ethyl, propyl, isopropyl, butyl, sec.butyl ortert.butyl.
 2. The enantiomeric D-configurations of the compoundsaccording to claim
 1. 3. The compound according to claim 1 which isN-(1'-ethoxycarbonyl-ethy)-N-methoxyacetyl-2,6-dimethylaniline.
 4. Thecompound according to claim 1 which isN-(1'-ethoxycarbonyl-ethyl)-N-methoxyacetyl-2-methyl-6-chloroaniline. 5.The compound according to claim 1 which isN-(1'-ethoxycarbonyl-ethyl)-N-methoxyacetyl-2,6-dichloroaniline.
 6. Amethod of combating phytophathogenic fungi which comprises applyingthereto a fungicidally effective amount of a compound according claim 1.7. The compoundN-('1-ethoxycarbonyl-ethyl)-N-methylthioacetyl-2,5-dichloroaniline. 8.The compoundN-(1'-ethoxycarbonyl-ethyl)-N-isopropylthioacetyl-2-methyl-6-ethylaniline.9. A fungicidal composition comprising as active substance afungicidally effective amount of a compound of the formula ##STR59##wherein R₂ represents methyl, ethyl or chlorine,each of R₇ and R₈independently represents hydrogen or methyl, and Y represents --OR₄ or--SR₄ in which R₄ represents methyl, ethyl, propyl, isopropyl, butyl,sec.butyl or tert.butyl, together with a suitable carrier therefor. 10.A composition according to claim 9 wherein the compound isN-(1'-ethoxycarbonyl-ethyl)-N-methoxyacetyl-2,6-dimethylaniline.
 11. Acomposition according to claim 9 wherein the compound isN-(1'-ethoxycarbonyl-ethyl)-N-methoxyacetyl-2-methyl-6-chloroaniline.12. A composition according to claim 9 wherein the compound isN-(1'-ethoxycarbonyl-ethyl)-N-isopropylthioacetyl-2-methyl-6-ethylaniline.13. A fungicidal composition comprising as active substance afungicidally effective amount of the compoundN-(1'-ethoxycarbonyl-ethyl)-N-methoxyacetyl-2,6-dichloroaniline,together with a suitable carrier therefor.
 14. A fungicidal compositioncomprising as active substance a fungicidally effective amount of thecompoundN-(1'-ethoxycarbonyl-ethyl)-N-methoxythioacetyl-2,5-dichloroaniline,together with a suitable carrier therefor.